Sulfamic Acid → HCID 69036013, compound

Temperature

23 °C

A Schlenk flask under argon was charged with {Ir(cod)Cl}2 (10 mg, 15 μmol, 3 mol %) and ligand (3,5-dioxa-4-phospha-cyclohepta[2,1-a; 3,4-a′]diphenyl-4-en)-dibenzo[b,f]azepine (12 mg, 30 μmol, 6 mol %). N,N-Dimethylformamide (2 mL) was added and the reaction mixture was stirred at 23° C. for 15 min. 5-Phenylpent-1-en-3-ol (81 mg, 0.50 mmol, 1 eq.) was added via syringe followed by the addition of solid sulfamic acid (49 mg, 0.50 mmol, 1 eq.). The resulting reaction mixture was heated to 50° C. Conversion was checked by disappearance of the starting material on TLC and/or by measuring 1H-NMR of an aliquot taken from the reaction mixture. After completion of the reaction (usually 3-4 hr), the reaction mixture was carefully concentrated and cooled to 23° C. The resulting brownish oil was redissolved in methylene chloride (3 mL), and Boc2O (202 mg, 1.00 mmol, 2 eq.) and a catalytic amount (ca. 10 mg) of the phase-transfer reagent n-Bu4NHSO4 were added at 0° C. At 0° C., the reaction mixture was treated with 0.5 M aqueous sodium hydroxide solution (3 mL) and warmed to 23° C. for 6 hr. Subsequently, the reaction mixture was partitioned between methylene chloride (10 mL) and water (10 mL). The aqueous layer was extracted with methylene chloride (3×15 mL). The combined organic layers were dried (sodium sulfate) and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel using hexanes/ethyl acetate as an eluent afforded the title compound (93 mg, 0.36 mmol, yield 71%) as an off-white solid.

1. customThe resulting reaction mixture
2. temperaturewas heated to 50° C
3. customAfter completion of the reaction (usually 3-4 hr), the reaction mixture
4. concentrationwas carefully concentrated
5. temperaturecooled to 23° C
6. dissolutionThe resulting brownish oil was redissolved in methylene chloride (3 mL)
7. temperaturewarmed to 23° C. for 6 hr
8. customSubsequently, the reaction mixture was partitioned between methylene chloride (10 mL) and water (10 mL)
9. extractionThe aqueous layer was extracted with methylene chloride (3×15 mL)
10. dry with materialThe combined organic layers were dried (sodium sulfate)
11. concentrationconcentrated under reduced pressure
12. customPurification of the residue by flash chromatography on silica gel

ORD record

ord-7e660fc21eee41f484bbb163df79a797

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863443B2